Crystal structures and Hirshfeld surface analyses of 2-[(4,6-di­amino­pyrimidin-2-yl)sulfan­yl]-N-(pyridin-2-yl)acetamide and 2-[(4,6-di­amino­pyrimidin-2-yl)sulfan­yl]-N-(pyrazin-2-yl)acetamide

The conformation of the title di­amino­pyrimidine sulfanly acetamides, (I) and (II), have similar conformations, with the pyrimidine ring being inclined to the pyridine ring in (I) by 71.10 (9) °, and by 62.93 (15) ° to the pyrazine ring in (II).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.094
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N1       --H1B            Please Check

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         14 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        42% Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0042 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1       --H1B            Please Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.874 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.196 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         25 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009).

2-[(4,6-Diaminopyrimidin-2-yl)sulfanyl]-N-(pyridin-2-yl)acetamide (I)

Crystal data

C11H12N6OS	Z = 2
Mr = 276.33	F(000) = 288
Triclinic, P1	Dx = 1.442 Mg m^−3
a = 7.2341 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3852 (2) Å	Cell parameters from 2605 reflections
c = 9.7971 (2) Å	θ = 2.1–26.4°
α = 95.820 (1)°	µ = 0.26 mm^−1
β = 91.116 (1)°	T = 293 K
γ = 105.682 (1)°	Block, yellow
V = 636.33 (3) Å^3	0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer	2160 reflections with I > 2σ(I)
Radiation source: X-ray	Rint = 0.020
ω and φ scans	θmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.742, Tmax = 0.841	k = −11→11
9447 measured reflections	l = −10→12
2605 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: mixed
wR(F^2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0443P)^2 + 0.1669P] where P = (Fo^2 + 2Fc^2)/3
2605 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.47564 (6)	0.24187 (5)	0.97878 (4)	0.04443 (15)
O1	0.1201 (2)	−0.07191 (14)	0.81504 (14)	0.0637 (4)
N1	0.4212 (3)	0.58093 (19)	0.63223 (17)	0.0509 (4)
H1A	0.470 (3)	0.652 (2)	0.584 (2)	0.059 (6)*
H1B	0.299 (3)	0.546 (2)	0.641 (2)	0.066 (7)*
N2	1.0373 (2)	0.60541 (19)	0.83751 (19)	0.0500 (4)
H2A	1.087 (3)	0.696 (2)	0.820 (2)	0.059 (6)*
H2B	1.092 (3)	0.590 (2)	0.914 (2)	0.071 (7)*
N3	0.45530 (19)	0.42030 (14)	0.78589 (14)	0.0378 (3)
N4	0.75997 (18)	0.44133 (14)	0.89781 (13)	0.0374 (3)
N5	0.2555 (2)	0.10689 (16)	0.67916 (14)	0.0395 (3)
H5	0.304 (3)	0.201 (2)	0.6830 (18)	0.046 (5)*
N6	0.3287 (2)	0.11118 (16)	0.45436 (15)	0.0458 (4)
C1	0.5404 (2)	0.53494 (17)	0.71413 (16)	0.0373 (4)
C2	0.7366 (2)	0.59919 (18)	0.72509 (17)	0.0398 (4)
H2	0.795008	0.672763	0.670694	0.048*
C3	0.8435 (2)	0.55043 (16)	0.81970 (16)	0.0367 (4)
C4	0.5717 (2)	0.38421 (16)	0.87394 (15)	0.0351 (4)
C5	0.2265 (2)	0.17793 (19)	0.91965 (17)	0.0452 (4)
H5A	0.149123	0.139634	0.994486	0.054*
H5B	0.185101	0.261192	0.891905	0.054*
C6	0.1943 (2)	0.05740 (18)	0.80001 (18)	0.0415 (4)
C7	0.2500 (2)	0.02603 (17)	0.55029 (17)	0.0369 (4)
C8	0.1697 (3)	−0.12615 (19)	0.5237 (2)	0.0506 (4)
H8	0.118824	−0.182978	0.593511	0.061*
C9	0.1674 (3)	−0.1909 (2)	0.3911 (2)	0.0603 (5)
H9	0.113148	−0.292746	0.369861	0.072*
C10	0.2447 (3)	−0.1056 (2)	0.2905 (2)	0.0574 (5)
H10	0.243138	−0.147400	0.200125	0.069*
C11	0.3246 (3)	0.0435 (2)	0.32694 (19)	0.0551 (5)
H11	0.379420	0.101358	0.258857	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0510 (3)	0.0393 (2)	0.0344 (2)	−0.00414 (19)	0.00358 (18)	0.00918 (17)
O1	0.0848 (10)	0.0348 (7)	0.0585 (8)	−0.0084 (6)	0.0102 (7)	0.0109 (6)
N1	0.0466 (10)	0.0522 (10)	0.0532 (10)	0.0079 (8)	−0.0012 (8)	0.0183 (8)
N2	0.0377 (8)	0.0444 (9)	0.0648 (11)	0.0003 (7)	0.0006 (7)	0.0222 (8)
N3	0.0399 (7)	0.0308 (7)	0.0382 (7)	0.0019 (6)	0.0022 (6)	0.0041 (5)
N4	0.0404 (8)	0.0310 (7)	0.0369 (7)	0.0020 (6)	0.0018 (6)	0.0064 (5)
N5	0.0438 (8)	0.0288 (7)	0.0397 (8)	−0.0008 (6)	0.0032 (6)	0.0044 (6)
N6	0.0523 (9)	0.0425 (8)	0.0418 (8)	0.0106 (7)	0.0039 (7)	0.0070 (6)
C1	0.0443 (9)	0.0331 (8)	0.0332 (8)	0.0084 (7)	0.0034 (7)	0.0030 (6)
C2	0.0427 (9)	0.0349 (8)	0.0411 (9)	0.0058 (7)	0.0085 (7)	0.0127 (7)
C3	0.0395 (9)	0.0281 (8)	0.0397 (9)	0.0042 (6)	0.0063 (7)	0.0040 (6)
C4	0.0427 (9)	0.0266 (7)	0.0311 (8)	0.0022 (6)	0.0056 (7)	−0.0004 (6)
C5	0.0451 (10)	0.0417 (9)	0.0412 (9)	−0.0018 (7)	0.0134 (8)	0.0050 (7)
C6	0.0385 (9)	0.0354 (9)	0.0458 (10)	0.0003 (7)	0.0037 (7)	0.0087 (7)
C7	0.0319 (8)	0.0358 (8)	0.0419 (9)	0.0079 (6)	−0.0010 (7)	0.0038 (7)
C8	0.0531 (11)	0.0375 (9)	0.0546 (11)	0.0026 (8)	0.0031 (9)	0.0009 (8)
C9	0.0629 (13)	0.0441 (11)	0.0672 (13)	0.0099 (9)	−0.0011 (10)	−0.0111 (9)
C10	0.0611 (12)	0.0643 (13)	0.0488 (11)	0.0266 (10)	−0.0007 (9)	−0.0100 (10)
C11	0.0636 (12)	0.0607 (12)	0.0436 (10)	0.0204 (10)	0.0081 (9)	0.0073 (9)

Geometric parameters (Å, º)

S1—C4	1.7682 (15)	N6—C7	1.332 (2)
S1—C5	1.8021 (18)	N6—C11	1.338 (2)
O1—C6	1.2124 (19)	C1—C2	1.381 (2)
N1—C1	1.348 (2)	C2—C3	1.384 (2)
N1—H1A	0.86 (2)	C2—H2	0.9300
N1—H1B	0.86 (2)	C5—C6	1.512 (2)
N2—C3	1.358 (2)	C5—H5A	0.9700
N2—H2A	0.86 (2)	C5—H5B	0.9700
N2—H2B	0.88 (2)	C7—C8	1.384 (2)
N3—C4	1.324 (2)	C8—C9	1.376 (3)
N3—C1	1.358 (2)	C8—H8	0.9300
N4—C4	1.328 (2)	C9—C10	1.365 (3)
N4—C3	1.3570 (19)	C9—H9	0.9300
N5—C6	1.354 (2)	C10—C11	1.368 (3)
N5—C7	1.400 (2)	C10—H10	0.9300
N5—H5	0.856 (19)	C11—H11	0.9300
C4—S1—C5	102.83 (8)	C6—C5—S1	111.72 (12)
C1—N1—H1A	118.3 (14)	C6—C5—H5A	109.3
C1—N1—H1B	117.3 (15)	S1—C5—H5A	109.3
H1A—N1—H1B	124 (2)	C6—C5—H5B	109.3
C3—N2—H2A	117.2 (13)	S1—C5—H5B	109.3
C3—N2—H2B	117.6 (15)	H5A—C5—H5B	107.9
H2A—N2—H2B	110 (2)	O1—C6—N5	124.47 (16)
C4—N3—C1	114.94 (13)	O1—C6—C5	121.07 (15)
C4—N4—C3	115.04 (13)	N5—C6—C5	114.46 (14)
C6—N5—C7	129.23 (14)	N6—C7—C8	123.05 (16)
C6—N5—H5	114.6 (12)	N6—C7—N5	112.92 (13)
C7—N5—H5	116.2 (12)	C8—C7—N5	124.02 (15)
C7—N6—C11	116.91 (15)	C9—C8—C7	118.03 (18)
N1—C1—N3	115.65 (15)	C9—C8—H8	121.0
N1—C1—C2	122.72 (15)	C7—C8—H8	121.0
N3—C1—C2	121.63 (15)	C10—C9—C8	120.00 (18)
C1—C2—C3	117.79 (14)	C10—C9—H9	120.0
C1—C2—H2	121.1	C8—C9—H9	120.0
C3—C2—H2	121.1	C9—C10—C11	117.86 (18)
N4—C3—N2	116.08 (15)	C9—C10—H10	121.1
N4—C3—C2	121.51 (14)	C11—C10—H10	121.1
N2—C3—C2	122.39 (15)	N6—C11—C10	124.13 (18)
N3—C4—N4	128.88 (14)	N6—C11—H11	117.9
N3—C4—S1	119.16 (12)	C10—C11—H11	117.9
N4—C4—S1	111.95 (12)
C4—N3—C1—N1	−174.86 (14)	C7—N5—C6—O1	−0.5 (3)
C4—N3—C1—C2	5.2 (2)	C7—N5—C6—C5	179.12 (15)
N1—C1—C2—C3	175.39 (15)	S1—C5—C6—O1	105.06 (17)
N3—C1—C2—C3	−4.7 (2)	S1—C5—C6—N5	−74.58 (17)
C4—N4—C3—N2	−176.87 (14)	C11—N6—C7—C8	1.2 (2)
C4—N4—C3—C2	1.5 (2)	C11—N6—C7—N5	−178.11 (15)
C1—C2—C3—N4	1.2 (2)	C6—N5—C7—N6	−178.11 (16)
C1—C2—C3—N2	179.38 (15)	C6—N5—C7—C8	2.5 (3)
C1—N3—C4—N4	−2.5 (2)	N6—C7—C8—C9	−1.7 (3)
C1—N3—C4—S1	177.30 (10)	N5—C7—C8—C9	177.57 (17)
C3—N4—C4—N3	−0.8 (2)	C7—C8—C9—C10	0.7 (3)
C3—N4—C4—S1	179.39 (10)	C8—C9—C10—C11	0.7 (3)
C5—S1—C4—N3	3.32 (14)	C7—N6—C11—C10	0.2 (3)
C5—S1—C4—N4	−176.85 (11)	C9—C10—C11—N6	−1.2 (3)
C4—S1—C5—C6	87.65 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N3	0.86 (2)	2.18 (2)	2.975 (2)	154 (2)
C8—H8···O1	0.93	2.31	2.894 (2)	121
N2—H2B···N4^i	0.88 (2)	2.20 (2)	3.082 (2)	178 (2)
N1—H1A···N6^ii	0.86 (2)	2.38 (2)	3.174 (2)	155 (2)
N2—H2A···O1^iii	0.86 (2)	2.13 (2)	2.956 (2)	159 (2)

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x+1, y+1, z.

2-[(4,6-Diaminopyrimidin-2-yl)sulfanyl]-N-(pyrazin-2-yl)acetamide (II)

Crystal data

C10H11N7OS	F(000) = 576
Mr = 277.32	Dx = 1.453 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.1333 (5) Å	Cell parameters from 3124 reflections
b = 8.1561 (3) Å	θ = 2.2–28.3°
c = 12.8442 (5) Å	µ = 0.26 mm^−1
β = 94.307 (3)°	T = 293 K
V = 1267.48 (9) Å^3	Block, yellow
Z = 4	0.28 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer	1320 reflections with I > 2σ(I)
Radiation source: X-ray	Rint = 0.084
ω and φ scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→12
Tmin = 0.723, Tmax = 0.863	k = −10→9
11968 measured reflections	l = −17→17
3124 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: mixed
wR(F^2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0452P)^2] where P = (Fo^2 + 2Fc^2)/3
3124 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.77107 (6)	0.20394 (11)	0.50448 (6)	0.0525 (3)
O1	1.06221 (18)	0.2503 (3)	0.55054 (17)	0.0779 (8)
N1	0.6951 (3)	0.2961 (4)	0.8740 (2)	0.0651 (9)
H1A	0.651 (3)	0.297 (4)	0.923 (3)	0.084 (13)*
H1B	0.760 (3)	0.342 (4)	0.881 (3)	0.079 (13)*
N2	0.4369 (2)	0.0046 (4)	0.6423 (3)	0.0635 (9)
H2A	0.391 (2)	−0.015 (4)	0.687 (2)	0.060 (11)*
H2B	0.423 (2)	−0.044 (4)	0.571 (3)	0.080 (11)*
N3	0.72886 (19)	0.2473 (3)	0.70403 (17)	0.0452 (7)
N4	0.59901 (19)	0.1011 (3)	0.58901 (17)	0.0463 (7)
N5	0.9712 (2)	0.1889 (3)	0.69294 (19)	0.0494 (7)
H5	0.912 (2)	0.197 (4)	0.719 (2)	0.057 (11)*
N6	1.0164 (2)	0.0445 (3)	0.84291 (19)	0.0545 (7)
N7	1.2266 (2)	−0.0273 (4)	0.7815 (2)	0.0659 (8)
C1	0.6580 (3)	0.2321 (4)	0.7813 (2)	0.0450 (8)
C2	0.5579 (2)	0.1540 (4)	0.7649 (2)	0.0466 (8)
H2	0.509877	0.146453	0.817830	0.056*
C3	0.5306 (2)	0.0872 (4)	0.6680 (2)	0.0438 (8)
C4	0.6909 (2)	0.1845 (4)	0.6132 (2)	0.0421 (7)
C5	0.8779 (2)	0.3427 (4)	0.5525 (2)	0.0497 (9)
H5A	0.897729	0.412594	0.495784	0.060*
H5B	0.849528	0.412281	0.605640	0.060*
C6	0.9796 (3)	0.2561 (4)	0.5981 (2)	0.0499 (9)
C7	1.0498 (2)	0.0968 (4)	0.7528 (2)	0.0440 (8)
C8	1.1544 (3)	0.0605 (4)	0.7222 (3)	0.0613 (10)
H8	1.174535	0.098921	0.658172	0.074*
C9	1.1922 (3)	−0.0808 (4)	0.8710 (3)	0.0610 (10)
H9	1.239366	−0.144894	0.914481	0.073*
C10	1.0895 (3)	−0.0446 (4)	0.9011 (2)	0.0598 (9)
H10	1.069630	−0.083866	0.965011	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0478 (5)	0.0731 (6)	0.0376 (4)	−0.0116 (5)	0.0092 (3)	−0.0006 (4)
O1	0.0459 (15)	0.134 (3)	0.0572 (14)	0.0005 (14)	0.0236 (12)	0.0208 (14)
N1	0.062 (2)	0.091 (2)	0.0445 (17)	−0.021 (2)	0.0163 (16)	−0.0161 (17)
N2	0.0446 (19)	0.090 (3)	0.0569 (19)	−0.0240 (17)	0.0124 (16)	−0.0020 (18)
N3	0.0437 (16)	0.0552 (19)	0.0379 (13)	−0.0049 (12)	0.0104 (12)	−0.0024 (12)
N4	0.0372 (15)	0.0617 (18)	0.0408 (14)	−0.0088 (14)	0.0095 (12)	−0.0002 (13)
N5	0.0379 (18)	0.069 (2)	0.0428 (15)	−0.0018 (16)	0.0162 (13)	0.0043 (14)
N6	0.0478 (17)	0.072 (2)	0.0447 (15)	0.0030 (15)	0.0119 (13)	0.0055 (14)
N7	0.0512 (19)	0.079 (2)	0.0690 (19)	0.0126 (17)	0.0169 (15)	0.0064 (17)
C1	0.049 (2)	0.046 (2)	0.0402 (16)	0.0041 (16)	0.0087 (15)	−0.0021 (15)
C2	0.042 (2)	0.058 (2)	0.0416 (17)	−0.0005 (17)	0.0110 (14)	0.0027 (15)
C3	0.0338 (19)	0.049 (2)	0.0493 (18)	0.0015 (16)	0.0076 (15)	0.0061 (16)
C4	0.0395 (19)	0.047 (2)	0.0410 (16)	0.0036 (16)	0.0083 (14)	0.0024 (15)
C5	0.047 (2)	0.055 (2)	0.0479 (18)	−0.0136 (16)	0.0103 (15)	0.0067 (15)
C6	0.044 (2)	0.061 (2)	0.0449 (18)	−0.0142 (17)	0.0067 (16)	0.0004 (16)
C7	0.0338 (19)	0.053 (2)	0.0463 (18)	−0.0016 (16)	0.0105 (15)	−0.0048 (16)
C8	0.053 (2)	0.076 (3)	0.057 (2)	0.007 (2)	0.0187 (18)	0.0088 (19)
C9	0.054 (2)	0.073 (3)	0.057 (2)	0.012 (2)	0.0051 (17)	0.0020 (19)
C10	0.061 (3)	0.069 (3)	0.0508 (19)	0.002 (2)	0.0107 (18)	0.0063 (19)

Geometric parameters (Å, º)

S1—C4	1.768 (3)	N6—C7	1.325 (3)
S1—C5	1.795 (3)	N6—C10	1.331 (4)
O1—C6	1.213 (3)	N7—C8	1.326 (4)
N1—C1	1.346 (4)	N7—C9	1.326 (4)
N1—H1A	0.86 (3)	C1—C2	1.374 (4)
N1—H1B	0.88 (3)	C2—C3	1.375 (4)
N2—C3	1.341 (4)	C2—H2	0.9300
N2—H2A	0.85 (3)	C5—C6	1.502 (4)
N2—H2B	1.00 (3)	C5—H5A	0.9700
N3—C4	1.325 (3)	C5—H5B	0.9700
N3—C1	1.367 (3)	C7—C8	1.389 (4)
N4—C4	1.323 (3)	C8—H8	0.9300
N4—C3	1.364 (3)	C9—C10	1.364 (4)
N5—C6	1.347 (4)	C9—H9	0.9300
N5—C7	1.398 (4)	C10—H10	0.9300
N5—H5	0.82 (3)
C4—S1—C5	102.17 (14)	N4—C4—S1	111.4 (2)
C1—N1—H1A	118 (2)	N3—C4—S1	119.0 (2)
C1—N1—H1B	120 (2)	C6—C5—S1	112.8 (2)
H1A—N1—H1B	122 (3)	C6—C5—H5A	109.0
C3—N2—H2A	121 (2)	S1—C5—H5A	109.0
C3—N2—H2B	120.4 (17)	C6—C5—H5B	109.0
H2A—N2—H2B	118 (3)	S1—C5—H5B	109.0
C4—N3—C1	114.1 (2)	H5A—C5—H5B	107.8
C4—N4—C3	114.7 (3)	O1—C6—N5	124.1 (3)
C6—N5—C7	128.4 (3)	O1—C6—C5	120.5 (3)
C6—N5—H5	118 (2)	N5—C6—C5	115.4 (3)
C7—N5—H5	114 (2)	N6—C7—C8	121.7 (3)
C7—N6—C10	115.5 (3)	N6—C7—N5	114.4 (3)
C8—N7—C9	116.0 (3)	C8—C7—N5	124.0 (3)
N1—C1—N3	114.9 (3)	N7—C8—C7	122.1 (3)
N1—C1—C2	123.3 (3)	N7—C8—H8	119.0
N3—C1—C2	121.9 (3)	C7—C8—H8	119.0
C1—C2—C3	118.2 (3)	N7—C9—C10	121.9 (3)
C1—C2—H2	120.9	N7—C9—H9	119.1
C3—C2—H2	120.9	C10—C9—H9	119.1
N2—C3—N4	114.2 (3)	N6—C10—C9	122.9 (3)
N2—C3—C2	124.3 (3)	N6—C10—H10	118.5
N4—C3—C2	121.4 (3)	C9—C10—H10	118.5
N4—C4—N3	129.6 (3)
C4—N3—C1—N1	−179.7 (3)	C7—N5—C6—O1	−2.8 (5)
C4—N3—C1—C2	1.7 (4)	C7—N5—C6—C5	177.6 (3)
N1—C1—C2—C3	−177.3 (3)	S1—C5—C6—O1	105.2 (3)
N3—C1—C2—C3	1.3 (5)	S1—C5—C6—N5	−75.2 (3)
C4—N4—C3—N2	179.0 (3)	C10—N6—C7—C8	−0.1 (5)
C4—N4—C3—C2	−0.9 (4)	C10—N6—C7—N5	179.5 (3)
C1—C2—C3—N2	178.4 (3)	C6—N5—C7—N6	−178.8 (3)
C1—C2—C3—N4	−1.7 (5)	C6—N5—C7—C8	0.8 (5)
C3—N4—C4—N3	4.6 (5)	C9—N7—C8—C7	1.1 (5)
C3—N4—C4—S1	−177.3 (2)	N6—C7—C8—N7	−0.4 (5)
C1—N3—C4—N4	−5.0 (5)	N5—C7—C8—N7	180.0 (3)
C1—N3—C4—S1	177.1 (2)	C8—N7—C9—C10	−1.3 (5)
C5—S1—C4—N4	172.4 (2)	C7—N6—C10—C9	−0.1 (5)
C5—S1—C4—N3	−9.3 (3)	N7—C9—C10—N6	0.9 (5)
C4—S1—C5—C6	93.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N3	0.82 (3)	2.25 (3)	2.993 (4)	151 (3)
C8—H8···O1	0.93	2.24	2.854 (4)	123
N2—H2B···N4^i	1.00 (3)	2.11 (3)	3.092 (4)	169 (3)
N1—H1A···O1^ii	0.86 (3)	2.06 (4)	2.904 (4)	167 (3)
N2—H2A···N7^iii	0.85 (3)	2.41 (3)	3.235 (4)	164 (3)
C9—H9···O1^iv	0.93	2.56	3.368 (4)	145

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1/2, −y+1/2, z+1/2; (iii) x−1, y, z; (iv) −x+5/2, y−1/2, −z+3/2.